Water → 4-[({[4-(Trifluoromethoxy)phenyl]amino}carbonyl)amino]-1-(cyclopropylmethyl)-1H-imidazole-2-carboxylic acid

HRID 2277414Notes

Reaction equation

HRID 2277414 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:26][CH:27]2[CH2:29][CH2:28]2)[CH:8]=[C:9]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)=[O:13])[N:10]=1)=[O:5])C.O.[OH-].[Na+]>C(O)C>[F:25][C:22]([F:23])([F:24])[O:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:12]([NH:11][C:9]2[N:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]([CH2:26][CH:27]3[CH2:28][CH2:29]3)[CH:8]=2)=[O:13])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 894520804-[({[4-(Trifluoromethoxy)phenyl]amino}carbonyl)amino]-1-(cyclopropylmethyl)-1H-imidazole-2-carboxylic acid ethyl ester

Product 1

HCID 594219534-[({[4-(Trifluoromethoxy)phenyl]amino}carbonyl)amino]-1-(cyclopropylmethyl)-1H-imidazole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.6 g (28.1 mmol) of 4-[({[4-(trifluoromethoxy)phenyl]amino}-carbonyl)amino]-1-(cyclopropylmethyl)-1H-imidazole-2-carboxylic acid ethyl ester is suspended in 158 ml of ethanol. While being cooled with ice, 16.4 ml of water and 6 ml (112 mmol) of 50% aqueous sodium hydroxide solution are added. The reaction mixture is stirred for 1 hour at room temperature and then concentrated by evaporation in a vacuum. The residue is taken up in 100 ml of isopropanol and mixed with 100 ml of 1N hydrochloric acid while being cooled with ice. The crystals are suctioned off and dried in a vacuum at 40° C.

Workup

  1. additionare added
  2. concentrationconcentrated by evaporation in a vacuum
  3. additionmixed with 100 ml of 1N hydrochloric acid
  4. temperaturewhile being cooled with ice
  5. customdried in a vacuum at 40° C.

Sources & evidence

ORD record
ord-9692a3a006574dca92d9f1c88565b1df
Source dataset
uspto-grants-2015_09
Patent number
US09133165B2

Reaction notes

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